Ester of substituted amino propyl alcohol



5 without undergoing decomposition.

Patented Nov. 20, 1923.

time? WERNER SCHULEMANN, 0F VOHWINKEL,

OF ELBEBFELD, GERMANY, ASSIGNORS TO FABBENFABRIKEN VORM. FRIEDRu' LU'DWIG SCHI TTZ AND KURT MEISENBURG,

BAYER AND 00., OF LEVERKUSEN, NEAR COLOGNE-ON-THE-RfiINE, GERMANY.

ESTER OF SUISTITUTED AMINO PROPYL ALCOHOL.

No Drawing. Application filed December To all whom it may concern:

Be it known that we, WERNER SCHULE- MANN, Lnnwrc Sorrii'rz, and KURT Mnrsannunc, citizens of Germany, residing at Voh- Winkel, Elberfeld, and Elberfeld, in the State of Prussia. Germany, have invented new and useful Improvements in Esters of Substituted Amino Propyl Alcohol, of which the following is a specification.

We have found that the hitherto unknown esters of alkylamines having most probably the following general formula:

(R meaning an alkyl) have proved tobe compounds possessing valuable anaesthetic properties.

The new products can be obtained by e'sterification of these alkamines with aromatic aminocarboxylic acids, e. g. aminobenzoic acid or aminocinnamic acid, e. g. by treatment with the para-nitrocinnamoylcholorid and reduction or by heating the alkamines with the alkylesters of para-aminobenzoic acid etc.

()ur new alkamine esters are generally amorphous solid products crystallizing from' ligroin, forming crystallized salts with acids which retain the valuable therapeutic properties oi the esters. The salts are soluble in water, the solutions being free from any irritating action and producing'local anaeslhosia. Th y can be boiled for sterilization An average single dose being about 0.005 to 0.5 gram for subcutaneous use.

In order to illustrate our new process more fully the following example is given, the parts being by wei htz-131 parts of alpha-methyl-beta-methy -gamma-dimethylamino propyl alcohol having most probably the following general formula H (CHah-N-CHr-CH-dI-OH Ha Ha are mixed with 500 parts of benzene and to the cooled solution a cold solution of 186 parts of paranitro-benzoylchlorid in benzene is added. The mixture is then heated for two hours on the water-bath, water'is added and the benzene is separated from 1, 1922. Serial No. 604,399.

the aqueous solution. By the addition of a sodium carbonate solution the para-nitrobenzoic acid ester of alpha-methyl-beta nicthyl-gamma-dimethylamino propyl alcohol separates.

For reduction one part ofit is dissolved in three parts of concentrated hydrochloric acid and to the solution heated to -60 C. one part of tin is added. During the reduction the temperature is kept at C. The solution is freed from tin by means of SH and from the filtered liquid the aminobase is separated by the addition of carbonate of potassium. It is an oil solidifying after some time. It melts at 8182 C. and forms a crystallized soluble salt with hydrochlorlc acid. The optically inactive product (racemic form) has two asymmetric carbon atoms. It can be resolved into its optically inactive isomers by a fractional crystallization of the base from ligroin or its salts from alcohol. The hydrochlorid of one of these products crystallizes in the shape of long needles melting at 216-217 0., the other forms crystals melting at 178 C.

Others of the above mentioned esters can be produced in an analogous wa e. g. the

- -para-aminobenzoic acid ester of a ha-ethyl- We claim:

1. The herein described new esters of alkaniines having most probably the following general formula:

(R meaning an alkyl), with an aromatic amino carboxylic acid, Which aminoesters have anaesthetic properties; being generally amorphous solid products crystallizmg from ligroin, forming crystallized salts with acids which retain the valuable therapeutic properties of the esters, these salts being soluble in 'Water and are free from any irritating action, substantially as described.

2. The herein described new para-aminobenzoic acid ester of alpha-methyl-betamethyl-gamma-dimethlamino propyl alcohol showing anaesthetic properties having most probably the following formula:

the racemic form melting at from 81-82 0., forming crystallized soluble salts with byset our hands.

WERNER SCHULEMANN. LUDWIG SCHUTZ. KURT MEISENBU G. 

